Enantioselective synthesis of chiral carbocyclic pyrimidine nucleosides via asymmetric cyclopropanation |
| |
| Affiliation: | 1. Key Laboratory for Green Chemical Process of Ministry of Education, School of Chemical Engineering & Pharmacy, Wuhan Institute of Technology, Wuhan 430205, China;2. Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205, China;3. Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, Zhengzhou 450001, China;4. School of Chemistry & Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, China;1. Department of Chemistry, Faculty of Pharmacy, Mersin University, 33169, Mersin, Turkey;2. School of Chemistry, Leeds University, Leeds, LS2 9JT, UK;3. Departamento de Química Orgánica, Instituto de Síntesis Orgánica (ISO) and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, E-03080, Alicante, Spain;1. School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, People’s Republic of China;2. The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University, Key Laboratory for Medical Data Analysis and Statistical Research of Tianjin, Tianjin 300071, People’s Republic of China;3. School of Chemistry and Chemical Engineering, Central South University, Changsha 410083, People’s Republic of China |
| |
| Abstract: | An efficient method to construct chiral cyclopropyl pyrimidine carbocyclic nucleoside analogues bearing a quaternary center was developed via asymmetric Michael-initiated cyclopropanation. The axis chirality was observed in cyclopropyl pyrimidine carbocyclic nucleoside analogues for the first time, which was caused by the rotationally restricted N C bond in N-COPh moiety. Using (DHQD)2AQN as the organocatalyst, diverse cyclopropyl pyrimidine carbocyclic nucleoside analogues were generated in 76–93% yields and 73–96% ee. |
| |
| Keywords: | Cyclopropanation Enantioselective Organocatalytic Pyrimidine nucleoside |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
